Synthesis of 3-Azidopiperidine Skeleton Employing Ceric Ammonium Nitrate (CAN)-Mediated Regioselective Azidoalkoxylation of Enol Ether: Total Synthesis of D2 Receptor Agonist (±)-Quinagolide
| Autor: | Subhash P. Chavan, Pradeep B. Lasonkar, Appasaheb L. Kadam, Rajesh G. Gonnade |
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| Rok vydání: | 2018 |
| Předmět: |
chemistry.chemical_classification
Nitroaldol reaction 010405 organic chemistry Chemistry Organic Chemistry Acetal food and beverages Total synthesis Regioselectivity 010402 general chemistry 01 natural sciences Biochemistry Medicinal chemistry 0104 chemical sciences Claisen rearrangement chemistry.chemical_compound Enol ether Pyridinium Physical and Theoretical Chemistry Ceric ammonium nitrate |
| Zdroj: | Organic Letters. 20:7011-7014 |
| ISSN: | 1523-7052 1523-7060 |
| DOI: | 10.1021/acs.orglett.8b02900 |
| Popis: | The total synthesis of (±)-quinagolide, which is a D2 receptor agonist, was accomplished via a ceric ammonium nitrate (CAN)-mediated regioselective azidoalkoxylation of enol ether route. Key features of the synthesis include Claisen rearrangement, PPTS (pyridinium p-toluenesulfonate)-catalyzed one-pot acetal deprotection, followed by a diastereoselective Henry reaction, which enables construction of the required trans ring junction and CAN-mediated regioselective azidoalkoxylation of enol ether. The PPTS-catalyzed intramolecular diastereoselective Henry reaction to fix three contiguous stereocenters on tetrahydronaphthalene and the first-of-its-kind synthesis of the 3-azidopiperidine skeleton, using a CAN-mediated regioselective azidoalkoxylation of enol ether, are important findings of the present work. |
| Databáze: | OpenAIRE |
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